D-A-D 2 H-benzo[ d][1,2,3]triazole derivatives as p-type semiconductors in organic field-effect transistors

Iván Torres-Moya; Iratxe Arrechea-Marcos; Carlos Tardío; José R Carrillo; Ángel Díaz-Ortiz; J Teodomiro López Navarrete; M Carmen Ruiz Delgado; Pilar Prieto; Rocío Ponce Ortiz

doi:10.1039/c8ra03246g

D-A-D 2 H-benzo[ d][1,2,3]triazole derivatives as p-type semiconductors in organic field-effect transistors

RSC Adv. 2018 Jun 13;8(39):21879-21888. doi: 10.1039/c8ra03246g.

Authors

Iván Torres-Moya¹, Iratxe Arrechea-Marcos², Carlos Tardío¹, José R Carrillo¹, Ángel Díaz-Ortiz¹, J Teodomiro López Navarrete², M Carmen Ruiz Delgado², Pilar Prieto¹, Rocío Ponce Ortiz²

Affiliations

¹ Department of Organic Chemistry, Faculty of Chemical and Technologies Sciences, University of Castilla La Mancha-IRICA 13071 Ciudad Real Spain MariaPilar.Prieto@uclm.es Ivan.TorresMoya@uclm.es.
² Department of Physical Chemistry, Faculty of Sciences, University of Málaga 29071 Málaga Spain rocioponce@uma.es.

Abstract

A series of Donor-π-Acceptor-π-Donor compounds based on a 2H-benzo[d][1,2,3]triazole core branched with different alkynyl donor groups has been characterized and tested in organic field-effect transistors (OFETs). The electronic and molecular structures were elucidated through optical and vibrational spectroscopy in conjunction with DFT calculations. The results indicate that the planarity of the structure and the good intramolecular charge transfer from the electron-donating to the electron-withdrawing fragments play a critical role in the application of the compounds as semiconductors in OFET devices. The compounds were tested in a top-contact/bottom-gate thin film transistor architecture, and they behave as p-type semiconductors.